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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Hillsdale vacation homes

Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is ￥16,905
￥22,500 total
includes taxes & fees
May 26 - May 27
All the comforts of home
Exterior

Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (11 reviews)
"We had an excellent experience. The place was wonderful. A real place to disconnect from everything. We Highly recommend it."
United States
Saul
The price is ￥25,469
￥53,809 total
includes taxes & fees
May 26 - May 27
Modern Luxurious Cabin, Catskills - The Tiny Nook
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is ￥24,211
￥62,592 total
includes taxes & fees
May 26 - May 27
Near Tanglewood: Historic Summer Retreat
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is ￥32,234
￥50,408 total
includes taxes & fees
May 27 - May 28
Cozy Riverside Berkshires Retreat
Desk, WiFi

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is ￥27,387
￥85,940 total
includes taxes & fees
May 26 - May 27
Charles Cottage Near Warren St New Renovation
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is ￥42,835
￥78,786 total
includes taxes & fees
May 27 - May 28
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is ￥32,632
￥72,917 total
includes taxes & fees
Jun 9 - Jun 10
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is ￥32,234
￥50,763 total
includes taxes & fees
May 26 - May 27
Home in Great Barrington
Terrace/patio

Lakefront Luxe Retreat | Beach, Pools, Pickleball

Lakefront Luxe Retreat | Beach, Pools, Pickleball
Athens
10.0 out of 10, Exceptional, (2 reviews)
"The house was wonderful. It was clean, well-appointed, and the kitchen was fully stocked. The neighborhood was great, too."
United States
Kevin M.
The price is ￥35,656
￥113,081 total
includes taxes & fees
May 26 - May 27
Lakefront Luxe Retreat | Beach, Pools, Pickleball
Interior

Brand New House w gated backyard that is located right at the Saugerties Village

Brand New House w gated backyard that is located right at the Saugerties Village
Saugerties
10.0 out of 10, Exceptional, (41 reviews)
"Great new and clean property! Very close to downtown, supermarket, and a short drive to Hunter Mountain & Kaaterskill falls. "
United States
Michael
The price is ￥30,085
￥67,747 total
includes taxes & fees
Jun 14 - Jun 15
Brand New House w gated backyard that is located right at the Saugerties Village
Exterior detail

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is ￥51,256
￥95,693 total
includes taxes & fees
Jun 1 - Jun 2
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
TV, offices

Catskill Stay w/ Deck & Fire Pit

Catskill Stay w/ Deck & Fire Pit
Catskill
9.0 out of 10, Wonderful, (4 reviews)
"Clean and comfortable house in a great location — and with fantastic communication. Highly recommend!"
United States
Cha R.
The price is ￥28,178
￥75,467 total
includes taxes & fees
May 26 - May 27
Catskill Stay w/ Deck & Fire Pit
Dining

Super Comfortable Water-view Home in Saugerties

Super Comfortable Water-view Home in Saugerties
Saugerties
9.8 out of 10, Exceptional, (6 reviews)
"Very comfortable home, everything that’s needed is there "
United States
gianni g.
The price is ￥48,152
￥128,853 total
includes taxes & fees
Jun 9 - Jun 10
Super Comfortable Water-view Home in Saugerties
Outdoor dining

Charming 2-bedroom Waterfront home with boat access in Saugerties

Charming 2-bedroom Waterfront home with boat access in Saugerties
Saugerties
9.6 out of 10, Exceptional, (12 reviews)
"Beautiful home, beautiful view, owner was great. Would absolutely book this residence again"
United States
Jeffrey B.
The price is ￥55,713
￥112,139 total
includes taxes & fees
May 31 - Jun 1
Charming 2-bedroom Waterfront home with boat access in Saugerties
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥37,726
￥80,369 total
includes taxes & fees
May 26 - May 27
Cheerful 3-bedroom cottage with woodstove
Interior

Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly

Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly
CATSKILL
9.4 out of 10, Exceptional, (3 reviews)
"Lovely short weekend in the countryside. Calm zen retreat surrounded by nature and animals."
United States
sarah j.
The price is ￥57,305
￥118,277 total
includes taxes & fees
Jun 1 - Jun 2
Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly
Fridge, microwave, oven, stovetop

Modern getaway in Catskills

Modern getaway in Catskills
Cairo
10.0 out of 10, Exceptional, (13 reviews)
"The host was accommodating and the house was very nice!"
United States
Ken B.
The price is ￥87,549
￥150,358 total
includes taxes & fees
May 26 - May 27
Modern getaway in Catskills
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥90,398
￥211,924 total
includes taxes & fees
May 31 - Jun 1
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (38 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is ￥73,223
￥134,776 total
includes taxes & fees
May 26 - May 27
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Fridge, microwave, stovetop, dishwasher

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is ￥27,857
￥89,498 total
includes taxes & fees
May 26 - May 27
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hillsdale Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Had a great stay at the Yankee Inn. I would definitely stay here again. Check in was great and super helpful for what to do and eat in the area. Carl at the bar was the best! Only complaint is that the fitted sheet kept coming up from our king mattress I had the fix them multiple times. Nice indoor pool and hot tub. Close to a lot."
Stacey 1-night trip
Posted 16 hours ago
The Yankee Inn

Find out more about Hillsdale

Hillsdale Vacation Homes information

Number of reviews
306
Accommodation
645 Vacation Homes
Lowest Price
￥22,500
Highest Price
￥211,924